Day 69: Hillary Weiss & Her Writing Style

So, yesterday I wrote headlines for Doug Paton’s post about storytelling & a bear. Today I’m writing for Hillary Weiss. She’s all kindsa content cray-cray and cranks her tone up to 11. She’s a brand voice superstah & has a distinct style you can see from across the internet.

I dig that about her.

I reached out to her about 2 recent pieces on Medium—one on voice, and one on pricing—and asked to create some headlines. Both were tough because Hillary’s style is way different than mine, and I had to get all up in her head space. But it was fun. Definitely not easy.

I talked to entrepreneurs about their business, but all they wanted to do was ask me about this

68

Don’t try to write without watching TV (and 6 other style tips)

69

Finding a writing style that fits you like a tailored suit

70

How to sound like you’re writing with your favorite pen

71

Do you need a writing stylist, or can you DIY our voice?

72

How to cram all the characters in your head into your hodgepodge of a writing style

73

How to write with style when you have none

74

My 10-year deep dive into writing style, summed up in 7 bullets

75

How much you should you edit out of your writing?

76

Turns out, your audience likes reading the same things as you

77

How I developed a writing style over 10 years by accident

78

7 writing tips that took me 10 years to perfect (as much as anyone can)

79

Is it better to sound smart, or sound like you?

80

The too-busy-to-learn writer’s guide to developing a personal style

81

7 tips (and 10 years of practice) to find your perfect writing voice

82

So, how much do you really have to write before you develop your style?

83

Stop thinking your audience is different than you—and write the way you want to

84

Here’s how to sound better when you write

85

Never buy a writing style off the rack

86

How much you should you put on the page?

87

Custom fitting your writing style like a wedding dress

88

How to write words that sound like people

89

What posting IN ALL CAPS taught me about my writing style

90

Who should you really write for? You or your audience?

91

Why you sound like X when you’re trying to sound like Y

92

How to make your writing sound like you

93

The DIY guide for writing style

94

How you can learn to write better by watching TV

95

How I stumbled into my writing style after only 28 years of practice

96

Writing like your audience may be dangerous if it doesn’t sound like you

97

Writing with style: It ain’t as easy it looks

98

How not to sound like everyone else on the internet

99

Get a writing style without losing you

100

What 10 years of writing for myself taught me about writing for other people

101

How I learned to write with style by accident

102

You’re not still trying to sound super smart when you write, are you?

103

What all the books about writing style I’ve never read have taught me

104

How to become a more stylized writer by not really trying

105

How to make your writing sound like jeans & a t-shirt

106

How much do you need to write before you start to develop your voice

107

How much of other people’s style can you put into your own voice?

108

The style guide for writing with personality

109

How I accidentally learned to write with style

110

The fastest way to write like you’ve been doing it all your life

111

Why your brand voice and your voice are two very different things

112

Your words sound funny. Did you do that on purpose?

113

My writing style was an accident—just like me

Overall: Whew! I don’t know if it was the challenge of writing to match her style, or the subject matter, but it took a tremendous effort to knock this out. I’m happy with the end results—and Hillary was too. Even if it took twice as long as usual.

Note, the italicized lines missed the mark. But the last one was really just for fun.

Lessons: Like yesterday, it was a tough to stay within the confines of the content. I think I did a better job today though.

There were a lot of good lines here. Just about any of them could work. The bold ones were Hillary’s favorites

I had to strike a balance between her voice and mine, with hers taking the lead

I kept wanting to explore new themes, like fashion, but that’s not part of the article. So I had to reel it in.

This is a great piece. It doesn’t need a new headline. This was just for fun